Benoxaprofen

Benoxaprofen, also known by its brand name Oraflex in the United States, is a nonsteroidal anti-inflammatory drug (NSAID) that was introduced in the 1980s. It belongs to the class of propionic acid derivatives, which includes other well-known NSAIDs such as ibuprofen and naproxen. Benoxaprofen works by inhibiting the enzyme cyclooxygenase (COX), which is involved in the synthesis of prostaglandins, substances that play a key role in inflammation, pain, and fever.

History

Benoxaprofen was developed by Eli Lilly and Company and was approved for medical use in the United Kingdom in 1980. It was marketed as a treatment for rheumatoid arthritis, osteoarthritis, and other conditions associated with pain and inflammation. Despite its initial promise, the drug was withdrawn from the market in 1982 due to serious side effects, including hepatotoxicity (liver damage), photosensitivity reactions, and, in some cases, death, particularly among elderly patients.

Mechanism of Action

As an NSAID, benoxaprofen's primary mechanism of action is the inhibition of the COX enzyme. By blocking COX-1 and COX-2 isoforms, it reduces the formation of prostaglandins, which are mediators of inflammation and pain. This action is similar to that of other NSAIDs, but benoxaprofen was noted for its long half-life, which allowed for once-daily dosing.

Adverse Effects

The adverse effects of benoxaprofen include gastrointestinal issues such as ulcers and bleeding, kidney dysfunction, and severe skin reactions due to photosensitivity. The most concerning side effect was its hepatotoxicity, which led to several reported cases of liver failure and death. The risk of these adverse effects, particularly in the elderly, led to the drug's withdrawal from the market.

Withdrawal from Market

The withdrawal of benoxaprofen is a notable example in the history of pharmaceutical regulation. It raised questions about the adequacy of drug testing and post-marketing surveillance, leading to increased scrutiny and changes in regulatory policies worldwide. The case of benoxaprofen highlighted the importance of monitoring drugs' safety profiles not only during clinical trials but also after they have been approved and are in widespread use.

Legacy

The benoxaprofen case had a lasting impact on the pharmaceutical industry and regulatory agencies. It underscored the need for rigorous post-marketing surveillance of drugs and contributed to the development of better pharmacovigilance practices. Despite its withdrawal, the story of benoxaprofen is often cited in discussions about drug safety, regulatory oversight, and the balance between the benefits and risks of pharmaceuticals.

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Benoxaprofen

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  Structures of benoxaprofen and psoralen

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  Benoxaprofen synthesis